CN108102029A - Production method of low-odor coumarone resin - Google Patents
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- CN108102029A CN108102029A CN201611043152.5A CN201611043152A CN108102029A CN 108102029 A CN108102029 A CN 108102029A CN 201611043152 A CN201611043152 A CN 201611043152A CN 108102029 A CN108102029 A CN 108102029A
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Abstract
The invention discloses a production method of low-odor coumarone resin, which is based on the traditional coumarone resin production process and is realized by changing the raw material composition, the decoloring method and the product post-treatment process. The method mainly comprises the steps of distilling raw materials, removing pyridine and phenol, decoloring and distilling, removing thiol, polymerizing, flashing, molecular distilling, curing and granulating to obtain the low-odor coumarone resin. The invention solves the environmental protection problems of solvent residue and the like, greatly reduces the solvent residue and has no obvious peculiar smell. The invention has simple operation, low residual oil content of the product, no peculiar smell and wide application, and is suitable for industrial production.
Description
Technical field
The invention belongs to chemical technology fields, are related to a kind of preparation method of coumarone indene resin, more particularly to a kind of low different
The preparation method of taste coumarone indene resin, and in particular to the producer of residual solvent and mercaptan etc. is reduced in a kind of coumarone indene resin
Method.
Background technology
Coumarone-indene resin is (referred to as:Coumarone indene resin) there is excellent acid resistance, alkali resistance, adherence, plasticising and benefit
The performances such as strong, are dissolved in chlorohydrocarbon, esters, ketone, ethers equal solvent, and have with various kinds of resin such as natural rubber, epoxy resin
Good compatibility is widely used by people as the modifying agent of various resins, is mainly used in coating, electronics for a long time
Material, adhesive, sealant, rubber, ink and other field,
In the prior art coumarone indene resin typical production process flow include distillation cutting fraction, pickling take off pyridine, polymerization,
The processes such as washing, curing, are finally made solid coumarone naval stores.As patent CN201110076405.X is disclosed：With coal
Tar is raw material, by de- weight, hydrogenation reaction, just point, dephenolize, de- pyridine, polymerize and etc. coumarone indene resin is made.Lu Jin
Longevity etc. " one indene resin of continuity method production high softening-point coumarone " text point out by distillation, pickling, dephenolize take off pyridine, decoloration,
Polymerization and flash distillation obtain the coumarone indene resin of 100-115 DEG C of softening point.Patent CN201410283274.6 discloses a kind of ancient horse
The method of grand resin removal of mercaptans, this method be in the coumarone production technology of existing coal chemical industry system, increase blow air, H2O2 and
NaClO washing process, mercaptans content is down to 20-25ppm from 60-90ppm before and after implementation.
To promote energy conservation and environmental protection, since China's air prevention and control situation needs further control volatile organic matter,
National Environmental Protection Agency puts into effect notice property tax (2015) 16, and VOC content surpasses 420g/L solvent based coatings and imposes 4% consumption tax.And
The Ministry of Industry and Information Technology and the Ministry of Finance dispatch a joint document on July 8th, 2016《The Ministry of Finance of the Ministry of Industry and Information Technology is on printing and distributing emphasis row
Industry volatile organic matter cuts down the notice of action plan》(Ministry of Industry and Information's interlink (2016) 217).Also specify coating, adhesive
Etc. low (nothing) the VOC products of industries, reduce solvent etc. target.
At present also containing a large amount of sources of odor in the coumarone indene resin product of technique productions, such as residual solvent oil or oligomer tree
Fat brings environmental issue to the follow-up use of product.If being improved to the production technology of coumarone indene resin, from raw material in advance from
The multi-angles such as reason, godied oil removal of mercaptans and product post processing are improved, and are substantially reduced the peculiar smell of product, are on the one hand improved
The peculiar smell of resin, being on the other hand then more advantageous to the environmental-protecting performance of the industries such as downstream coating, adhesive improves, and improves coumarone tree
The environmentally friendly performance of fat.
The content of the invention
The present invention is to provide a kind of production method of low peculiar smell coumarone indene resin on the basis of existing technology.It solves existing
The Peculiar Smell of product, the present invention is easy to operate, product residua content is few, and free from extraneous odour is suitable for industrialized production.
Technical scheme is as follows：
A kind of production method of low peculiar smell coumarone indene resin, which is characterized in that include the following steps：
(1) raw material distills：Raw material cuts boiling point in 135-195 DEG C of fraction by destilling tower, obtains thick coumarone fraction；
(2) thick coumarone fraction takes off pyridine dephenolize：Pyridine dephenolize is taken off by conventional pickling and alkali washing method, in further
Sum arrives C2SN；
(3) decoloration distillation：By the C2SN oil of de- pyridine dephenolize by bleaching tower, heavy fraction is isolated from bottom of towe；From tower
Bleached oil C3SN is steamed on top；
(4) removal of mercaptans：It is filled in activated carbon or zeolite fixed-bed reactor, carries out removal of mercaptans processing, obtain polymerizeing
Feedstock oil CSN；
(5) it polymerize：It obtains mixing with catalyst for the feedstock oil CSN of polymerization by above-mentioned, be gathered at 50-150 DEG C
It closes 0.5-2h and obtains godied oil PSN；
(6) flash：It is flashed after godied oil PSN is washed, obtains coumarone indene resin；
(7) molecular distillation：Coumarone indene resin after flash distillation is subjected to molecular distillation, obtains the coumarone indene resin of low peculiar smell.
Further, the step (1) raw material distillation enrichment can poly group divide while, by controlling reflux ratio 3-7m3/ h,
Light oil and heavy oil are eliminated as much as, naphthalene content is made to be less than 3%.
Further, the activated carbon described in step (4) or molecular sieve can be the activated carbon or molecular sieve of supported active agent, institute
Supported active agent is stated as metal ion.
Further, the metal ion is Cu2+And/or Pb2+。
Further, the technological parameter of the step (4)：110-170 DEG C of temperature, air speed 1h-1-7.0h-1。
The device of step (7) molecular distillation distills for level-one.Further, molecular distillation condition is：Vacuum degree 0.1~
20kPa, 130~260 DEG C of vapo(u)rizing temperature, knifing 250~400rpm of revolution, 20~50 DEG C of cryosurface temperature.
The heavy fraction of the step (3) contains containing naphthalene, acid tar oil, pitch.
Further above-mentioned steps further include curing and are granulated：Liquid coumarone indene resin under the condition of high temperature is uniform through nodulizer
It is distributed on steel band, the water cooled particulate resins that are made enter packaging.
Detailed description of the invention
Method critical process provided by the invention is：First raw material (thick indenes) distill, by distill in raw material can
Poly group point (can poly group point refer to that the active component that can be polymerize such as indenes, methyl indenes, styrene, coumarone etc. contain double bond
Aromatic hydrocarbons or alkene) be enriched with, while control naphthalene content be less than 3%.Second：Removal of mercaptans system；It is filled in removal of mercaptans tower
Activated carbon or molecular sieve can remove mercaptan etc.；3rd, molecular distillation removal coumarone indene resin residual solvent and oligomer tree
Fat.
The technical scheme comprises the following steps in detail：
1) raw material distills：Raw material cuts boiling point in 135-195 DEG C of fraction by destilling tower, obtains thick coumarone fraction
RCSN.Enrichment can poly group while divide, remove light oil and heavy oil.
2) thick coumarone fraction takes off pyridine dephenolize：Pyridine dephenolize is taken off by conventional pickling and alkali washing method, in further
Sum arrives C2SN.
3) decoloration distillation：By the C2SN oil of de- pyridine dephenolize by bleaching tower, from bottom of towe isolate containing naphthalene, acid tar oil,
The heavy fractions such as pitch.Polymer raw oil, i.e. bleached oil C3SN are steamed from tower top.
4) removal of mercaptans：It is filled in activated carbon or zeolite fixed-bed reactor, carries out removal of mercaptans processing, obtain for polymerization
Feedstock oil CSN.
5) it polymerize：CSN with catalyst is mixed, polymerase 10 .5-2h is carried out at 50-150 DEG C and obtains godied oil；
6) flash：It is flashed after godied oil PSN is washed, removes the impurity without polymerizeing, obtain coumarone indene resin.
7) molecular distillation：Coumarone indene resin after flash distillation is subjected to molecular distillation, deviates from residual solvent and oligomer resin,
Obtain the coumarone indene resin of low peculiar smell.
8) cure and be granulated：Liquid coumarone indene resin under the condition of high temperature is evenly distributed on through nodulizer on steel band, through water
The cold particulate resins that are made enter packaging.
Further, step 1) enrichment can poly group while divide, by controlling reflux ratio 3-7m3/ h, is eliminated as much as light oil
And heavy oil, naphthalene content is made to be less than 3%.
Activated carbon or molecular sieve described in step 4) can be preferably the activated carbon or molecular sieve of supported active agent, be loaded
Metal ion such as Cu2+, Pb2+Deng.Purpose is removing mercaptan etc., more effectively to reduce the peculiar smell of coumarone indene resin.Technique
Parameter：110-170 DEG C of temperature, air speed 1h-1-7.0h-1。
Molecular distillation described in step 7), it is therefore an objective to which the further remaining solvent of removing and oligomer resin finally obtain
Low peculiar smell coumarone indene resin.Molecular distillation apparatus distills for level-one.Molecular distillation condition is：0.1~20kPa of vacuum degree, distillation
130~260 DEG C of temperature, knifing 250~400rpm of revolution, 20~50 DEG C of cryosurface temperature.
The invention discloses a kind of production methods of low peculiar smell coumarone indene resin, are in traditional coumarone indene resin production
It on Process ba- sis, is made up of feed change, discoloration method and product aftertreatment technology, solves the environmental protection such as its dissolvent residual and ask
Topic, substantially reduces dissolvent residual, product is without apparent peculiar smell.The present invention is easy to operate, product residua content is few, free from extraneous odour, application
Extensively, it is suitable for industrialized production.
Compared with prior art, advantage for present invention and effect are：
(1) the invention discloses a kind of production method of low peculiar smell coumarone indene resin, by controlling raw material composition, removal of mercaptans
With product aftertreatment technology, the environmental issues such as its dissolvent residual are solved, substantially reduce dissolvent residual, product is without apparent peculiar smell.
(2) present invention increases process in original technology, easy to operate, be suitable for industrialized production.Product Residual oil
Content is few, free from extraneous odour, more meets environmental requirement, therefore in coating, adhesive and ink etc. application are wider, low different by this
Taste technique significantly improves its application value.
Description of the drawings
Fig. 1 is the production technological process of low peculiar smell coumarone indene resin.
Specific embodiment
With reference to embodiment, the present invention is further elaborated, it will be appreciated by those skilled in the art that the embodiment
It is given for example only, without forming any restrictions to the present invention.
The production method technological process of the present invention as shown in Figure 1, raw material through distilling, de- pyridine dephenolize, decoloration distillation, desulfurization
Alcohol, polymerization, flash distillation, molecular distillation and curing, which are granulated, obtains low peculiar smell coumarone indene resin.
The technical solution further illustrated the present invention with reference to embodiment.
Embodiment one：
Raw material enters destilling tower, and the thick coumarone RCSN that 135~195 DEG C of boiling spreads are cut in Distallation systm evaporates
Part, control reflux ratio 4m3/ h, tower top obtain thick coumarone fraction, and chromatography detection naphthalene content is 2.38%.Thick coumarone fraction into
Enter descaling bath, at normal temperatures, neutralized using 40% dilute sulfuric acid cycle pickling by the RCSN of pickling twice with 1O%NaOH, so
Neutrality is obtained with water washing afterwards and obtains material C2SN.Washed material C2SN enters bleaching tower, l1O DEG C of top of tower temperature,
Pressure 17.3kPa, further impurity such as naphtalene oil removed in material etc., tower top obtains bleached oil C3SN.Bleached oil C3SN enters
Fixed bed reactors are at mercaptan-eliminating catalyst CuX molecular sieves, 110 DEG C, air speed 5h-1, under normal pressure, obtain removal of mercaptans oil CSN, sulphur
Alcohol content 5ppm.CSN is polymerize to obtain godied oil at catalyst BF3,85 DEG C.Godied oil enters flash system,
30Kpa, 140 DEG C of tower top temperature carry out vacuum flashing at 210 DEG C of column bottom temperature, and obtained flash oil enters molecular distillation system,
In vacuum degree 20kPa, 250 DEG C of temperature, prolapse solvent and oligomer resin, low peculiar smell coumarone is obtained by cooling granulation
Resin, 100 DEG C, molecular weight MW61O of softening point, residua content 0.08%, naphthalene content 22ppm.
Contrast experiment：Raw material enters destilling tower, and the thick ancient horse of 135~195 DEG C of boiling spreads is cut in Distallation systm
Grand RCSN fractions, tower top obtain thick coumarone fraction, and chromatography detection naphthalene content is 4.38%.Thick coumarone fraction enters pickling
Slot at normal temperatures, is neutralized, then with water using 40% dilute sulfuric acid cycle pickling by the RCSN of pickling twice with 1O%NaOH
Washing obtains neutrality and obtains material C2SN.Washed material C2SN enters bleaching tower, in l1O DEG C of top of tower temperature, pressure
17.3kPa, further impurity such as naphtalene oil removed in material etc., tower top obtains bleached oil C3SN, mercaptans content 50.70ppm.
C3SN is polymerize to obtain godied oil at catalyst BF3,85 DEG C.Godied oil enters flash system, in 30Kpa, tower top temperature
140 DEG C, vacuum flashing is carried out at 210 DEG C of column bottom temperature, prolapse solvent obtains low peculiar smell coumarone tree by cooling granulation
Fat, 89.1 DEG C, molecular weight MW591 of softening point, residua content 3.68%, naphthalene content 0.3%.
It can be seen that from above-mentioned experimental result and control naphthalene content, mercaptan-eliminating catalyst and molecular distillation distilled using raw material
Method, the mercaptans content of obtained low peculiar smell coumarone indene resin drops to 5ppm from 50.71ppm, and naphthalene content is reduced to from 0.3%
22ppm, residual oil content are reduced to 0.08% from 3.68%, and the peculiar smell of coumarone indene resin substantially reduces.
Embodiment two：
Raw material enters destilling tower, and the thick coumarone RCSN that 135~195 DEG C of boiling spreads are cut in Distallation systm evaporates
Part, control reflux ratio 4.5m3/ h, tower top obtain thick coumarone fraction, and chromatography detection naphthalene content is 2.01%.Thick coumarone fraction
Into descaling bath, at normal temperatures, neutralized using 40% dilute sulfuric acid cycle pickling by the RCSN of pickling twice with 1O%NaOH,
Then neutrality is obtained with water washing and obtains material C2SN.Washed material C2SN enters bleaching tower, in top of tower temperature l1O
DEG C, pressure 17.3kPa, further remove impurity such as naphtalene oil etc. in material, tower top obtains bleached oil C3SN.Bleached oil C3SN into
Enter fixed bed reactors at mercaptan-eliminating catalyst CuX molecular sieves, 110 DEG C, air speed 4h-1, under normal pressure, removal of mercaptans oil CSN is obtained,
Mercaptans content 4ppm.CSN is polymerize to obtain godied oil at catalyst BF3,80 DEG C.Godied oil enters flash system,
30Kpa, 140 DEG C of tower top temperature carry out vacuum flashing at 210 DEG C of column bottom temperature, and obtained flash oil enters molecular distillation system,
In vacuum degree 15kPa, 230 DEG C of temperature, prolapse solvent and oligomer resin, low peculiar smell coumarone is obtained by cooling granulation
Resin, 134 DEG C, molecular weight MW915 of softening point, residua content 0.05%, naphthalene content 18ppm.
Contrast experiment：Raw material enters destilling tower, and the thick ancient horse of 135~195 DEG C of boiling spreads is cut in Distallation systm
Grand RCSN fractions, tower top obtain thick coumarone fraction, and chromatography detection naphthalene content is 3.74%.Thick coumarone fraction enters pickling
Slot at normal temperatures, is neutralized, then with water using 40% dilute sulfuric acid cycle pickling by the RCSN of pickling twice with 1O%NaOH
Washing obtains neutrality and obtains material C2SN.Washed material C2SN enters bleaching tower, in l1O DEG C of top of tower temperature, pressure
17.3kPa, further impurity such as naphtalene oil removed in material etc., tower top obtains bleached oil C3SN, mercaptans content 57.08ppm.
C3SN is polymerize to obtain godied oil at catalyst BF3,80 DEG C.Godied oil enters flash system, in 30Kpa, tower top temperature
140 DEG C, vacuum flashing is carried out at 210 DEG C of column bottom temperature, prolapse solvent obtains low peculiar smell coumarone tree by cooling granulation
Fat, 107.2 DEG C, molecular weight MW829 of softening point, residua content 2.10%, naphthalene content 0.2%.
It can be seen that from above-mentioned experimental result and control naphthalene content, mercaptan-eliminating catalyst and molecular distillation distilled using raw material
Method, the mercaptans content of obtained low peculiar smell coumarone indene resin drops to 4ppm from 57.08ppm, and naphthalene content is reduced to from 0.2%
18ppm, residual oil content are reduced to 0.06% from 2.10%, and the peculiar smell of coumarone indene resin substantially reduces.
Embodiment three：
Raw material enters destilling tower, and the thick coumarone RCSN that 135~195 DEG C of boiling spreads are cut in Distallation systm evaporates
Part, control reflux ratio 5m3/ h, tower top obtain thick coumarone fraction, and chromatography detection naphthalene content is 1.38%.Thick coumarone fraction into
Enter descaling bath, at normal temperatures, neutralized using 40% dilute sulfuric acid cycle pickling by the RCSN of pickling twice with 1O%NaOH, so
Neutrality is obtained with water washing afterwards and obtains material C2SN.Washed material C2SN enters bleaching tower, l1O DEG C of top of tower temperature,
Pressure 17.3kPa, further impurity such as naphtalene oil removed in material etc., tower top obtains bleached oil C3SN.Bleached oil C3SN enters
Fixed bed reactors are at mercaptan-eliminating catalyst CuX molecular sieves, 120 DEG C, air speed 3h-1, under normal pressure, obtain removal of mercaptans oil CSN, sulphur
Alcohol content 2ppm.CSN is polymerize to obtain godied oil at catalyst BF3,70 DEG C.Godied oil enters flash system,
30Kpa, 140 DEG C of tower top temperature carry out vacuum flashing at 210 DEG C of column bottom temperature, and obtained flash oil enters molecular distillation system,
In vacuum degree 10kPa, 250 DEG C of temperature, prolapse solvent and oligomer resin, low peculiar smell coumarone is obtained by cooling granulation
Resin, 145 DEG C, molecular weight MW977 of softening point, residua content 0.02%, naphthalene content 12ppm.
Contrast experiment：Raw material enters destilling tower, and the thick ancient horse of 135~195 DEG C of boiling spreads is cut in Distallation systm
Grand RCSN fractions, tower top obtain thick coumarone fraction, and chromatography detection naphthalene content is 3.45%.Thick coumarone fraction enters pickling
Slot at normal temperatures, is neutralized, then with water using 40% dilute sulfuric acid cycle pickling by the RCSN of pickling twice with 1O%NaOH
Washing obtains neutrality and obtains material C2SN.Washed material C2SN enters bleaching tower, in l1O DEG C of top of tower temperature, pressure
17.3kPa, further impurity such as naphtalene oil removed in material etc., tower top obtains bleached oil C3SN, mercaptans content 55.20ppm.
C3SN is polymerize to obtain godied oil at catalyst BF3,70 DEG C.Godied oil enters flash system, in 30Kpa, tower top temperature
140 DEG C, vacuum flashing is carried out at 210 DEG C of column bottom temperature, prolapse solvent obtains low peculiar smell coumarone tree by cooling granulation
Fat, 114.6 DEG C, molecular weight MW852 of softening point, residua content 1.75%, naphthalene content 0.18%.
It can be seen that from above-mentioned experimental result and control naphthalene content, mercaptan-eliminating catalyst and molecular distillation distilled using raw material
Method, the mercaptans content of obtained low peculiar smell coumarone indene resin drops to 2ppm from 55.20ppm, and naphthalene content is reduced from 0.18%
To 12ppm, residual oil content is reduced to 0.02% from 1.75%, and the peculiar smell of coumarone indene resin substantially reduces.
1 embodiment of table summarizes
Claims (9)
1. a kind of production method of low peculiar smell coumarone indene resin, which is characterized in that include the following steps：
(1) raw material distills：Raw material cuts boiling point in 135-195 DEG C of fraction by destilling tower, obtains thick coumarone fraction；
(2) thick coumarone fraction takes off pyridine dephenolize：Pyridine dephenolize is taken off by conventional pickling and alkali washing method, is further neutralized
To C2SN；
(3) decoloration distillation：By the C2SN oil of de- pyridine dephenolize by bleaching tower, heavy fraction is isolated from bottom of towe；From tower top
Steam bleached oil C3SN；
(4) removal of mercaptans：It is filled in activated carbon or zeolite fixed-bed reactor, carries out removal of mercaptans processing, obtain the original for polymerization
Expect oil CSN；
(5) it polymerize：It obtains mixing with catalyst for the feedstock oil CSN of polymerization by above-mentioned, be polymerize at 50-150 DEG C
0.5-2h obtains godied oil PSN；
(6) flash：It is flashed after godied oil PSN is washed, obtains coumarone indene resin；
(7) molecular distillation：Coumarone indene resin after flash distillation is subjected to molecular distillation, obtains the coumarone indene resin of low peculiar smell.
2. a kind of production method of low peculiar smell coumarone indene resin according to claim 1, which is characterized in that in the step
(1) raw material distillation enrichment can poly group while divide, by controlling reflux ratio 3-7m3/ h, is eliminated as much as light oil and heavy oil, makes naphthalene
Content is less than 3%.
3. a kind of production method of low peculiar smell coumarone indene resin according to claim 1, which is characterized in that step (4) is described
Activated carbon or molecular sieve can be supported active agent activated carbon or molecular sieve, the supported active agent be metal ion.
A kind of 4. production method of low peculiar smell coumarone indene resin according to claim 3, which is characterized in that the metal ion
For Cu2+And/or Pb2+。
A kind of 5. production method of low peculiar smell coumarone indene resin according to claim 1, which is characterized in that the step (4)
Technological parameter：110-170 DEG C of temperature, air speed 1h-1-7.0h-1。
A kind of 6. production method of low peculiar smell coumarone indene resin according to claim 1, which is characterized in that the step (7)
The device of molecular distillation distills for level-one.
A kind of 7. production method of low peculiar smell coumarone indene resin according to claim 1, which is characterized in that the step (7)
Molecular distillation condition is：0.1~20kPa of vacuum degree, 130~260 DEG C of vapo(u)rizing temperature, knifing 250~400rpm of revolution, cryosurface
20~50 DEG C of temperature.
A kind of 8. production method of low peculiar smell coumarone indene resin according to claim 1, which is characterized in that the step (3)
Heavy fraction contain containing naphthalene, acid tar oil, pitch.
9. a kind of production method of low peculiar smell coumarone indene resin according to claim 1, which is characterized in that the step is also wrapped
Curing is included to be granulated：Liquid coumarone indene resin under the condition of high temperature is evenly distributed on through nodulizer on steel band, it is water cooled to be made
Granular resin enters packaging.
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| CN110128243A (en) * | 2019-06-05 | 2019-08-16 | 恒河材料科技股份有限公司 | A method of propylene glycol in weight alcohol waste liquid is recycled using extraction |
| CN112300326A (en) * | 2019-07-26 | 2021-02-02 | 宝武炭材料科技有限公司 | Method for improving hydroxyl value of coumarone resin and application |
| CN114057938A (en) * | 2020-08-05 | 2022-02-18 | 宝武炭材料科技有限公司 | Modified liquid coumarone resin and preparation method thereof |
| CN114057939A (en) * | 2020-08-05 | 2022-02-18 | 宝武炭材料科技有限公司 | Modified liquid resin and preparation method thereof |
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